It is well known that pinolenic acid (=5,9,12 C18:3 fatty acid i.e. a fatty acid with 18 C atoms having three double bonds in the positions 5, 9 and 12) is present in e.g. pine nut oil or fractions thereof in amounts of up to about 25 wt %. (cf e.g. J Am Oil Chem Soc 1998, 75, p.45-50). It is also known that pine nut oil (and thus pinolenic acid) can be applied in food products (cf e.g. Fr 2 756 465 wherein the use of a concentrate with 15% pinolenic in food additives is disclosed. The presence of pinolenic acid provides a hypolipemic effect to the composition). Further the prior art indicates that pinolenic acid derivatives have a number of health benefits. E.g. WO 9843513 discloses that nail files can be coated with pinolenic acid and that this inhibits the occurrence of infections upon use of the files.
According to JP 61238729 pine oil can be used as anticholesterimic agent. Other documents wherein health effects of pinolenic acid are disclosed are:
Japanese Patent Application 61058536, wherein a very generic activity beneficial for human health is disclosed; Sugano c.s in Brit J. of Nutr 72 (1994) 775-783, wherein hypocholesterolaemic effects, effects on ADP-induced platelet aggregation, on aortic prostacylic production and on blood pressure are reported while Matsuo discloses in Prostagl, Leukotrienes and Essential fatty Acids 55 (1996) 223-229 effects on CD-4xe2x80x3-lymphocytes and on CD8+-subsets.
However none of the prior art documents indicate that pinolenic acid could have anti-inflammatory properties. We performed a study in order to find compounds with anti-inflammatory properties. This study resulted in the finding that pinolenic acid can be used as an anti-inflammatory agent. Therefore our invention concerns in the first instance the use of a composition, preferably in the form of a food supplement, a pharmaceutical composition or a food composition, comprising 1.5 to 100 wt %, preferably 5 to 80 wt %, most preferably 10 to 50 wt % of pinolenic acid and wherein the composition is used as an anti-inflammatory agent.
An efficient way to administer an effective dose of the anti-inflammatory component is to administer a food supplement to the consumer. Therefore our invention also concerns food supplements with anti-inflammatory properties comprising a composition with 1.5 to 100 wt %, preferably 5 to 80 wt %, most preferably 10 to 50 wt % of pinolenic acid, which supplements preferably comprise a component, containing pinolenic acid, in encapsulated form in a food grade encapsulating material. The component containing the pinolenic acid can be selected from free fatty acid mixtures or from glyceride mixtures or from mixtures hereof. The glyceride mixture used preferably is derived from pine nut oil or concentrates thereof, in particular a concentrate of pine nut oil with a content of pinolenic acid of more than 28 wt % is applied. The encapsulating material can be any food grade material that according to prior art methods can be used in encapsulated food products.
According to another embodiment concentrates of pinolenic acid, wherein the concentrate comprises 28 to 60 wt % of pinolenic acid, 10 to 60 wt % of linoleic acid, 5 to 52 wt % of oleic acid, while its trans plus saturated fatty acid content is less than 10 wt % are also part of the invention. In these concentrates the pinolenic acid and other fatty acids can be present as free acids and/or in the form of mono- and/or di- and/or triglycerides. These concentrates can be applied in food products or they first can be blended with other components in order to achieve a structuring effect upon use in a food product. Therefore part of the invention are also blends of a composition (A), containing pinolenic acid and one or more other components (B), wherein the composition (A) comprises 1.5 to 100 wt % of pinolenic acid, while the other components (B) are selected from glycerides comprising linoleic acid and/or oleic acid and/or trans acids and/or saturated fatty acids while (A) and (B) have a preselected composition and are present in such ratios that the final blend contains:
0 to 70 wt %, preferably 25 to 65 wt % (trans plus saturated fatty acids), while the trans content preferably is less than 10 wt %;
1.5 to 60 wt % of pinolenic acid and
25 to 85 wt % of (linoleic plus oleic acid).
These blends can be applied beneficially in food products as healthy fat compounds.
Preferred blends are blends wherein composition (A) is a concentrate according to the invention and wherein the components (B) are selected from the group consisting of:
i) liquid oils, such as soybean oil; sunflower oil; rape seed oil and cotton seed oil
ii) cocoa butter or cocoa butter equivalents
iii) palm oil or fractions thereof
iv) enzymically made fats
v) fish oils or fractions thereof
vi) conjugated linoleic acid or enriched isomer mixtures thereof
vii) gamma linoleic acid or enriched mixtures thereof
viii)hardened liquid oils
ix) mixtures of one or more of components i) to viii).
Above blends preferably display solid fat contents measured by NMR-pulse on non stabilized fats of: N20=1-80, preferably 5-45 N35 less than 20, preferably less than 10, most preferably less than 5. Non stablised meaning that the fat was melted at 80xc2x0 C., cooled to 0xc2x0 C. and held at 0xc2x0 C. for 30 min, whereupon the fat was heated to measurement temperature and held thereon for 30 min before measuring the N value. The concentrates according to the invention can be prepared by a process wherein an enzymic hydrolysis or glycerolysis is performed using an enzyme that can discrimate between fatty acids with a delta 5 double bond and other fatty acids. Therefore this process involves the preparation of a concentrate of pinolenic acid having more than 28 wt % pinolenic acid by:
i) reacting a glyceride material containing at least 2 wt % of fatty acid with a cis5 double bond with water or glycerol in the presence of an enzyme capable of discriminating between fatty acids containing a delta double bond and other fatty acids
ii) splitting the reaction mixture into a partial glyceride rich component and a fatty acid rich component
iii) optionally converting the fatty acid rich component of step ii) to triglycerides by reaction with glycerol in the presence of a suitable enzyme
iv) optionally splitting the partial glyceride rich material of step ii) into components that are i) rich in monoglycerides, ii) rich in diglycerides and iii) rich in triglycerides and then optionally converting the partial glycerides i) and ii) into triglycerides by reaction with fatty acids in the presence of a suitable enzyme.